Fungicide n-(3-phenylpropyl) carboxamide derivatives

ABSTRACT

A compound of general formula (I): 
     
       
         
         
             
             
         
       
     
     A process for preparing this compound. 
     A fungicidal composition comprising a compound of general formula (I). 
     A method for treating plants by applying a compound of general formula (I) or a composition comprising it.

The present invention relates to fungicide N-(3-phenylpropyl)carboxamidederivatives, their thiocarboxamide or N-substituted carboximidamideanalogues, their process of preparation, their use as fungicides,particularly in the form of fungicidal compositions, and methods for thecontrol of phytopathogenic fungi of plants using these compounds ortheir compositions.

International Patent Application WO 2005/066138 discloses heterocyclicamide derivatives of general formula and their use as fungicides.Compounds according to the present invention are not disclosed in thatpatent application.

International Patent Application WO 2000/76979 discloses 2-pyridinecarboxamide derivatives of general formula encompassing general formulaof compounds according to the present invention and their use asfungicides. Compounds according to the present invention are notdisclosed in that patent application.

It is always of high-interest in the field of agrochemicals to usepesticidal compounds more active than the compounds already known by theman ordinary skilled in the art whereby less compound can be used whilstretaining equivalent efficacy.

Furthermore, the provision of new pesticidal compounds with a higherefficacy strongly reduces the risk of appearance of resistant strains inthe fungi to be treated.

We have now found a new family of compounds which show enhancedfungicidal activity over the general known family of such compounds.

Accordingly, the present invention relates to aN-(3-phenylpropyl)carboxamide derivative of general formula (I)

in which:

n is 1, 2, 3, 4 or 5;

T represents O, S, N—R^(a), N—OR^(b), N—NR^(a)R^(b) or N—CN;

X is a halogen atom, a nitro group, a cyano group, a hydroxy group, anamino group, a sulfanyl group, a pentafluoro- ⁶-sulfanyl group, a formylgroup, a formyloxy group, a formylamino group, a carboxy group, acarbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₁-C₈-alkylamino, a di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, aC₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, a C₁-C₈-alkylsulfanyl,a C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, aC₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogenatoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5halogen atoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to 5halogen atoms, a C₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylsulphonyl, aC₁-C₈-halogenoalkylsulphonyl having 1 to 5 halogen atoms, aC₁-C₆-alkoxyimino, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a (benzyloxyimino)-C₁-C₆-alkyl, abenzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanylor a phenylamino;

R¹ and R² are chosen independently of each other as being a hydrogenatom, a halogen atom, a C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms,a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms;

R³ and R⁴ are chosen independently of each other as being a hydrogenatom, a halogen atom, a C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms,a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms;

R⁵ and R⁸ are chosen independently of each other as being a hydrogenatom, a C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₈-alkyl,a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms;

R⁷ is a hydrogen atom, a C₁-C₈-alkyl or a C₃-C₇-cycloalkyl;

R^(a) and R^(b), that can be the same or different, represent a hydrogenatom; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; C₁-C₈-alkoxy-C₁-C₈-alkyl;C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl comprising up to 9 halogen atomsthat can be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynylcomprising up to 9 halogen atoms that can be the same or different;C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-halogenocycloalkylcomprising up to 9 halogen atoms that can be the same or different;formyl; C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising upto 9 halogen atoms that can be the same or different;C₁-C₈-alkylsulphonyl; C₁-C₈-halogenoalkylsulphonyl comprising up to 9halogen atoms that can be the same or different; phenyl that can besubstituted by up to 5 groups Q; naphthyl that can be substituted by upto 6 groups Q; phenylmethylene that can be substituted by up to 5 groupsQ; phenylsulphonyl that can be substituted by up to 5 groups Q;

Q, that can be the same or different, represents a halogen atom; cyano;nitro; C₁-C₈-alkyl; C₁-C₈-alkoxy; C₁-C₈-alkylsulfanyl;C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different; tri(C₁-C₈)alkylsilyl andtri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl; C₁-C₈-alkoxyimino;(C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; and

Het represents a 5-, 6- or 7-membered non-fused heterocycle with one,two or three heteroatoms which may be the same or different, Het beinglinked by a carbon atom and Het being substituted in ortho-position byat least one substituant linked by a carbon atom and optionallysubstituted in any other position by one or further substituents chosenfrom a halogen atom, a nitro group, a pentafluoro-6-sulfanyl group, aformyl group, a formyloxy group, a formylamino group, a carboxy group, aC₁-C₈-alkyl, a C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, aC₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkoxyhaving 1 to 5 halogen atoms, a C₁-C₈-alkoxy-C₂-C₈-alkenyl, aC₁-C₈-alkylsulfanyl, a C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogenatoms, a C₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1to 5 halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to 5halogen atoms, a C₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinylhaving 1 to 5 halogen atoms, a C₁-C₈-alkyl-sulphonyl, aC₁-C₈-halogenoalkylsulphonyl having 1 to 5 halogen atoms or aC₁-C₈-alkylsulfonamide;

as well as its salts, N-oxydes, metallic complexes, metalloidiccomplexes and optically active isomers;

with the proviso that compound of formula (I) is different from:

-   4,6-dichloro-2-(methylthio)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,-   4-chloro-2-(methylthio)-6-[(2-phenylethyl)amino]-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,-   4-chloro-2-(methylthio)-6-[(2-phenylmethyl)amino]-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,-   4-chloro-2-(methylthio)-6-(phenylamino)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,-   4-chloro-2-(methylthio)-6-[(2-phenylpropyl)amino]-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,-   5-chloro-1-methyl-N-(3-phenylpropyl)-1H-pyrazole-4-carboxamide,-   N-[3-(4-acetyl    phenyl)propyl]-5-chloro-3-methoxythiophene-2-carboxamide, and-   4-(3-{[(5-chloro-3-methoxy-2-thienyl)carbonyl]amino}propyl)benzoic    acid.

In the context of the present invention:

halogen means fluorine, bromine, chlorine or iodine.

carboxy means —C(═O)OH;

carbonyl means —C(═O)—;

carbamoyl means —C(═O)NH₂;

N-hydroxycarbamoyl means —C(═O)NHOH;

an alkyl group, an alkenyl group, and an alkynyl group as well asmoieties containing these terms, can be linear or branched; and

heteroatom means sulphur, nitrogen or oxygen.

in the case of an amino group or the amino moiety of any otheramino-comprising group, substituted by two substituents that can be thesame or different, the two substituents together with the nitrogen atomto which they are linked can form a heterocyclyl group, preferably a 5-to 7-membered heterocyclyl group, that can be substituted or that caninclude other hetero atoms, for example a morpholino group orpiperidinyl group.

Any of the compounds of the present invention can exist in one or moreoptical or chiral isomer forms depending on the number of asymmetriccentres in the compound. The invention thus relates equally to all theoptical isomers and to their racemic or scalemic mixtures (the term“scalemic” denotes a mixture of enantiomers in different proportions),and to the mixtures of all the possible stereoisomers, in allproportions. The diastereoisomers and/or the optical isomers can beseparated according to the methods which are known per se by the manordinary skilled in the art.

Any of the compounds of the present invention can also exist in one ormore geometric isomer forms depending on the number of double bonds inthe compound. The invention thus relates equally to all geometricisomers and to all possible mixtures, in all proportions. The geometricisomers can be separated according to general methods, which are knownper se by the man ordinary skilled in the art.

Any of the compounds of general formula (I) wherein X represents ahydroxy, a sulfanyl group or an amino group may be found in itstautomeric form resulting from the shift of the proton of said hydroxy,sulfanyl or amino group. Such tautomeric forms of such compounds arealso part of the present invention. More generally speaking, alltautomeric forms of compounds of general formula (I) wherein Xrepresents a hydroxy, a sulfanyl group or an amino group, as well as thetautomeric forms of the compounds which can optionally be used asintermediates in the preparation processes, and which will be defined inthe description of these processes, are also part of the presentinvention.

According to the present invention, the phenyl moiety of compound ofgeneral formula (I) may be substituted in any position by (X)_(n), X andn being as defined above. Preferably, the present invention relates toN-(3-phenylpropyl)carboxamide derivative or its thiocarboxamide, ofgeneral formula (I) in which the different characteristics may be chosenalone or in combination as being:

as regards n, n is 1 or 2;

as regards T, T is O or S.

as regards X, X is chosen as being a halogen atom, a(hydroxyimino)-C₁-C₈-alkyl group, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₆-alkoxyimino, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl or a (benzyloxyimino)-C₁-C₆-alkyl.

According to the present invention, the carbon atoms of the propylicmoiety, of compound of formula (I) are substituted by R¹, R², R³, R⁴, R⁵and R⁶; R¹, R², R³, R⁴, R⁵ and R⁶ being as defined above. Preferably,the present invention also relates to N-(3-phenylpropyl)carboxamidederivative, its thiocarboxamide, of general formula (I) in which inwhich the different characteristics may be chosen alone or incombination as being:

as regards R¹ and R², R¹ and R² are respectively chosen independently ofeach other as being a hydrogen atom or a C₁-C₈-alkyl;

as regards R³ and R⁴, R³ and R⁴ are respectively chosen independently ofeach other as being a hydrogen atom or a C₁-C₈-alkyl; and

as regards R⁵ and R⁶, R⁵ and R⁶ are respectively chosen independently ofeach other as being a hydrogen atom or a C₁-C₈-alkyl.

According to the present invention, the nitrogen atom of the carboxamideor the thiocarboxamide or the carboximidamide moiety of the compound offormula (I) is substituted by R⁷, R⁷ being a hydrogen atom, aC₁-C₈-alkyl or a C₃-C₇-cycloalkyl. Preferably, the C₃-C₇-cycloalkyl iscyclopropyl.

According to the present invention, “Het” of the compound of generalformula (I) is a 5-, 6- or 7-membered non-fused heterocycle with one,two or three heteroatoms which may be the same or different, Het beinglinked by a carbon atom and being substituted at least in ortho positionby at least one substituant linked by a carbon atom. Preferably, thepresent invention also relates to N-methyl carboxamide derivative, itsthiocarboxamide or N-substituted carboximidamide analogue, of generalformula (I) in which the different characteristics may be chosen aloneor in combination as being:

Het is chosen as being 2-furan, 3-furan, 4,5-dihydro-3-furan,2-thiophene, 3-thiophene, 2-pyrrole, 3-pyrrole, 5-oxazole, 4-oxazole,5-thiazole, 4-thiazole, 5-pyrazole, 4-pyrazole, 3-pyrazole, 3-isoxazole,4-isoxazole, 5-isoxazole, 4-isothiazole, 4-1,2,3-triazole,4-thiadiazole, 5-1,2,3-thiadiazole, 4,5-dihydro-4-pyrazole, 2-pyridine,3-pyridine, 4-pyridine, 1,4-oxathiine, 3,4-dihydro-5-pyran,2,3-dihydro-1,4-oxathiine, or 2-pyrazine;

Het is substituted in ortho position by a halogen atom, a C₁-C₈-alkyl ora C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms; and

Het is substituted in any other position by a hydrogen atom, a halogenatom, a C₁-C₈-alkyl, an amino group, a C₁-C₈-alkylamino or adi-C₁-C₈-alkylamino. More preferably, Het is substituted in any otherposition by a hydrogen atom or a halogen atom.

According to the present invention, “Het” of the compound of generalformula (I) may be a five membered ring heterocycle. Specific examplesof compounds of the present invention where Het is a five memberedheterocycle include:

Het represents a heterocycle of the general formula (Het-1)

-   -   in which:

R⁸ and R⁹ may be the same or different and may be a hydrogen atom, ahalogen atom, an amino group, a nitro group, a C₁-C₄-alkyl or aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms; and

R¹⁰ may be a halogen atom, a nitro group, a C₁-C₄-alkyl or aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-2)

-   -   in which:

R¹¹ may be a hydrogen atom, a halogen atom, a C₁-C₄-alkyl or aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms; and

R¹² and R¹³ may be the same or different and may be a hydrogen atom, ahalogen atom, an amino group, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkylhaving 1 to 5 halogen atoms;

provided that the R¹¹ and R¹³ are not both a hydrogen atom.

Het represents a heterocycle of the general formula (Het-3)

-   -   in which:

R¹⁴ may be a halogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms; and

R¹⁵ may be a hydrogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkylhaving 1 to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-4)

-   -   in which:

R¹⁶ and R'⁷ may be the same or different and may be a hydrogen atom, ahalogen atom, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having 1 to 5 halogenatoms, a C₁-C₄-alkylthio or a C₁-C₄-alkylsulphonyl; and

R¹⁸ may be a halogen atom, a cyano group, a C₁-C₄-alkyl, aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms or aC₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-5)

-   -   in which:

R¹⁹ and R²⁰ may be the same or different and may be a hydrogen atom, ahalogen atom, a C₁-C₄-alkyl, a C₁-C₄-alkyloxy or a C₁-C₄-halogenoalkylhaving 1 to 5 halogen atoms; and

R²¹ may be a hydrogen atom, a halogen atom, a C₁-C₄-alkyl or aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms;

provided that the R²⁰ and R²¹ are not both a hydrogen atom.

Het represents a heterocycle of the general formula (Het-6)

-   -   in which:

R²² may be a hydrogen atom, a halogen atom, a cyano group, a C₁-C₄-alkylor a C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms;

R²³ and R²⁵ may be the same or different and may be a hydrogen atom, ahalogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having 1 to 5halogen atoms; and

R²⁴ may be a hydrogen atom, a cyano group, a C₁-C₄-alkyl, aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, aC₁-C₄-alkoxy-C₁-C₄-alkyl, a hydroxy-C₁-C₄-alkyl, a C₁-C₄-alkylsulphonyl,a di(C₁-C₄-alkyl)aminosulphonyl or a C₁-C₆-alkylcarbonyl;

provided that the R²² and R²⁵ are not both a hydrogen atom.

Het represents a heterocycle of the general formula (Het-7)

-   -   in which:

R²⁶ may be a hydrogen atom, a cyano group, a C₁-C₄-alkyl, aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, aC₁-C₄-alkoxy-C₁-C₄-alkyl, a hydroxy-C₁-C₄-alkyl, a C₁-C₄-alkylsulphonyl,a di(C₁-C₄-alkyl)aminosulphonyl or a C₁-C₆-alkylcarbonyl; and

R²⁷ and R²⁸ may be the same or different and may be a hydrogen atom, ahalogen atom, a cyano group, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms or a C₁-C₄-alkylcarbonyl;

R²⁹ may be a halogen atom, a cyano group, a C₁-C₄-alkyl, aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms or aC₁-C₄-alkylcarbonyl;

Het represents a heterocycle of the general formula (Het-8)

-   -   in which:

R³⁰ may be a hydrogen atom or a C₁-C₄-alkyl; and

R³¹ may be a halogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-9)

-   -   in which:

R³² may be a hydrogen atom or a C₁-C₄-alkyl; and

R³³ may be a halogen atom, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having 1to 5 halogen atoms or a phenyl optionally substituted by a halogen atomor a C₁-C₄-alkyl.

Het represents a heterocycle of the general formula (Het-10)

-   -   in which:

R³⁴ may be a hydrogen atom, a halogen atom, an amino group, a cyanogroup, a C₁-C₄-alkylamino, a di-(C₁-C₄-alkyl)amino, a C₁-C₄-alkyl or aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms; and

R³⁵ may be a halogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-11)

-   -   in which:

R³⁶ may be a hydrogen atom, a halogen atom, an amino group, a cyanogroup, a C₁-C₄-alkylamino, a di-(C₁-C₄-alkyl)amino, a C₁-C₄-alkyl or aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms; and

R³⁷ may be a halogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-12)

-   -   in which:

R³⁸ may be a halogen atom, a cyano group, a nitro group, a C₁-C₄-alkyl,a C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, a C₃-C₆-cycloalkyl, aC₁-C₄-alkoxy, a C₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms, aC₁-C₄-alkylthio, a C₁-C₄-halogenoalkylthio having 1 to 5 halogen atoms,an aminocarbonyl group or an aminocarbonyl-C₁-C₄-alkyl;

R³⁹ may be a hydrogen atom, a halogen atom, a cyano group, a nitrogroup, a C₁-C₄-alkyl, a C₁-C₄-alkoxy or a C₁-C₄-alkylthio; and

R⁴⁰ may be a hydrogen atom, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms, a hydroxy-C₁-C₄-alkyl, a C₂-C₆-alkenyl, aC₃-C₆-cycloalkyl, a C₁-C₄-alkylthio-C₁-C₄-alkyl, aC₁-C₄-halogenoalkylthio-C₁-C₄-alkyl having 1 to 5 halogen atoms, aC₁-C₄-alkoxy-C₁-C₄-alkyl or a C₁-C₄-halogenoalkoxy-C₁-C₄-alkyl having 1to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-13)

-   -   in which:

R⁴¹ may be a hydrogen atom, a halogen atom, a cyano group, a nitrogroup, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms,a C₃-C₆-cycloalkyl, a C₁-C₄-alkoxy, a C₁-C₄-halogenoalkoxy having 1 to 5halogen atoms, a C₁-C₄-alkylthio, a C₁-C₄-halogenoalkylthio having 1 to5 halogen atoms, an aminocarbonyl or an aminocarbonyl-C₁-C₄-alkyl;

R⁴² may be a hydrogen atom, a halogen atom, a cyano group, aC₁-C₄-alkyl, a C₁-C₄-alkoxy, a C₁-C₄-halogenoalkoxy having 1 to 5halogen atoms or a C₁-C₄-alkylthio; and

R⁴³ may be a hydrogen atom, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms, a hydroxy-C₁-C₄-alkyl, a C₂-C₆-alkenyl, aC₃-C₆-cycloalkyl, a C₁-C₄-alkylthio-C₁-C₄-alkyl, aC₁-C₄-halogenoalkylthio-C₁-C₄-alkyl having 1 to 5 halogen atoms, aC₁-C₄-alkoxy-C₁-C₄-alkyl, a C₁-C₄-halogenoalkoxy-C₁-C₄-alkyl having 1 to5 halogen atoms or a phenyl optionally substituted by a halogen atom, aC₁-C₄-alkyl, a C₁-C₄-alkoxyalkyl or a nitro group;

provided that the R⁴¹ and R⁴² are not both a hydrogen atom.

Het represents a heterocycle of the general formula (Het-14)

-   -   in which:

R⁴⁴ may be a hydrogen atom, a halogen atom, a cyano group, a nitrogroup, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms,a C₃-C₆-cycloalkyl, a C₁-C₄-alkoxy, a C₁-C₄-halogenoalkoxy having 1 to 5halogen atoms, a C₁-C₄-alkylthio, a C₁-C₄-halogenoalkylthio having 1 to5 halogen atoms, an aminocarbonyl, or an aminocarbonyl-C₁-C₄-alkyl;

R⁴⁵ may a halogen atom, a cyano group, a C₁-C₄-alkyl, a C₁-C₄-alkoxy, aC₁-C₄-alkylthio or a C₁-C₄-halogenoalky having 1 to 5 halogen atoms;

R⁴⁶ may be a hydrogen atom, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms, a hydroxy-C₁-C₄-alkyl, a C₂-C₆-alkenyl, aC₃-C₆-cycloalkyl, a C₁-C₄-alkylthio-C₁-C₄-alkyl, aC₁-C₄-halogenoalkylthio-C₁-C₄-alkyl having 1 to 5 halogen atoms, aC₁-C₄-alkoxy-C₁-C₄-alkyl, a C₁-C₄-halogenoalkoxy-C₁-C₄-alkyl having 1 to5 halogen atoms;

Het represents a heterocycle of the general formula (Het-15)

-   -   in which:

R⁴⁷ may be a hydrogen atom, a halogen atom, a C₁-C₄-alkyl or aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms; and

R⁴⁸ may be a halogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-16)

in which R⁴⁹ and R⁵⁰ may be the same or different and may be a hydrogenatom, a halogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having 1 to5 halogen atoms;

provided that R⁴⁹ and R⁵⁰ are not both a hydrogen atom.

Het represents a heterocycle of the general formula (Het-17)

-   -   in which

R⁵¹ may be a halogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms. and

R⁵² may be a halogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-18)

in which R⁵³ may be a halogen atom, a C₁-C₄-alkyl or aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-19)

-   -   in which:

R⁵⁴ may be a halogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms; and

R⁵⁵ may be a hydrogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkylhaving 1 to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-20)

in which R⁵⁶ may be a halogen atom, a C₁-C₄-alkyl or aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms.

Het represents a heterocycle of the general formula (Het-21)

-   -   in which:

R⁵⁷ may be a hydrogen atom, a halogen atom, a cyano group, a nitrogroup, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms,a C₃-C₆-cycloalkyl, a C₁-C₄-alkoxy, a C₁-C₄-halogenoalkoxy having 1 to 5halogen atoms, a C₁-C₄-alkylthio, a C₁-C₄-halogenoalkylthio having 1 to5 halogen atoms, an aminocarbonyl or an aminocarbonyl-C₁-C₄-alkyl; and

R⁵⁸ may be a hydrogen atom, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having1 to 5 halogen atoms, a hydroxy-C₁-C₄-alkyl, a C₂-C₆-alkenyl, aC₃-C₆-cycloalkyl, a C₁-C₄-alkylthio-C₁-C₄-alkyl, aC₁-C₄-halogenoalkylthio-C₁-C₄-alkyl having 1 to 5 halogen atoms, aC₁-C₄-alkoxy-C₁-C₄-alkyl, a C₁-C₄-halogenoalkoxy-C₁-C₄-alkyl having 1 to5 halogen atoms or a phenyl optionally substituted by a halogen atom, aC₁-C₄-alkyl, a C₁-C₄-alkoxyalkyl or a nitro group;

According to the present invention, “Het” of the compound of generalformula (I) may be a six membered ring heterocycle. Specific examples ofcompounds of the present invention where Het is a six memberedheterocycle include:

Het represents a heterocycle of the general formula (Het-22)

-   -   in which:

R⁵⁹ may be a halogen atom, a hydroxy group, a cyano group, aC₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, aC₁-C₄-alkoxy, a C₁-C₄-alkylthio, a C₁-C₄-halogenoalkylthio having 1 to 5halogen atoms or a C₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms; and

R⁶⁰, R⁶¹ and R⁶², which may be the same or different, may be a hydrogenatom, a halogen atom, a cyano group, a C₁-C₄-alkyl, aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₄-alkoxy, aC₁-C₄-alkylthio, a C₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms, aC₁-C₄-alkylsulphinyl or a C₁-C₄-alkylsulphonyl.

Het represents a heterocycle of the general formula (Het-23)

-   -   in which:

R⁶³ may be a hydrogen atom, a halogen atom, a hydroxy group, a cyanogroup, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms,a C₁-C₄-alkoxy, a C₁-C₅-alkylthio, a C₂-C₅-alkenylthio aC₁-C₄-halogenoalkylthio having 1 to 5 halogen atoms or aC₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms;

R⁶⁴, R⁶⁵ and R⁶⁶, which may the same or different, may be a hydrogenatom, a halogen atom, a cyano group, a C₁-C₄-alkyl, aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₄-alkoxy, aC₁-C₄-alkylthio, a C₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms, aC₁-C₄-alkylsulphinyl or a C₁-C₄-alkylsulphonyl;

provided that the R⁶³ and R⁶⁶ are not both a hydrogen atom.

Het represents a heterocycle of the general formula (Het-24)

-   -   in which:

R⁶⁷, R⁶⁸, R⁶⁹ and R⁷⁰, which may be the same or different, may be ahydrogen atom, a halogen atom, a hydroxy group, a cyano group, aC₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, aC₁-C₄-alkoxy, a C₁-C₄-alkylthio, a C₁-C₄-halogenoalkylthio having 1 to 5halogen atoms, a C₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms, aC₁-C₄-alkylsulphinyl or a C₁-C₄-alkylsulphonyl;

provided that the R⁶⁷ and R⁷⁰ are not both a hydrogen atom.

Het represents a heterocycle of the general formula (Het-25)

-   -   in which:

Q¹ may be a sulphur atom, —SO— or —SO₂—;

R⁷¹ may be a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having 1 to 5 halogenatoms; and

R⁷² and R⁷³ may be the same or different and may be a hydrogen atom or aC₁-C₄-alkyl.

Het represents a heterocycle of the general formula (Het-26)

-   -   in which:

Q¹ may be a sulphur atom, —SO—, —SO₂— or —CH₂—;

R⁷⁴ may be a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having 1 to 5 halogenatoms; and

R⁷⁵ and R⁷⁶ may be the same or different and may be a hydrogen atom or aC₁-C₄-alkyl.

Het represents a heterocycle of the general formula (Het-27)

in which R⁷⁷ may be a halogen atom, a C₁-C₄-alkyl or aC₁-C₄-halogenoalkyl having 1 to 5 halogen atoms.

The present invention also relates to a process for the preparation ofthe compound of general formula (I). Thus, according to a further aspectof the present invention there is provided a process P1 for thepreparation of compound of general formula (I) wherein T represents O,as defined above, which comprises reacting a 3-phenylpropan-1-aminederivative of general formula (II) or one of its salt:

in which X, n, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are as defined above; witha carboxylic acid derivative of the general formula (III)

in which:

Het is as defined above; and

L¹ is a leaving group chosen as being a halogen atom, a hydroxyl group,—OR^(c), —OCOR^(c), R^(c) being a C₁-C₆ alkyl, a C₁-C₆ haloalkyl, abenzyl, 4-methoxybenzyl, pentafluorophenyl or a

in the presence of a catalyst and, if L' is a hydroxyl group, in thepresence of a condensing agent.

The process according to the present invention is conducted in thepresence of a catalyst. Suitable catalyst may be chosen as being4-dimethyl-aminopyridine, 1-hydroxy-benzotriazole or dimethylformamide.

In case L¹ is a hydroxy group, the process according to the presentinvention is conducted in the presence of condensing agent. Suitablecondensing agent may be chosen as being acid halide former, such asphosgene, phosphorous tribromide, phosphorous trichloride,phosphorous-pentachloride, phosphorous trichloride oxide or thionylchloride; anhydride former, such as ethyl chloroformate, methylchloroformate, isopropyl chloroformate, isobutyl chloroformate ormethanesulfonyl-chloride; carbodiimides, such asN,N′-dicyclohexylcarbodiimide (DCC) or other customary condensingagents, such as phosphorous pentoxide, polyphosphoric acid,N,N′-carbonyl-diimidazole,2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/tetrachloromethane,4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloridehydrate or bromo-tripyrrolidino-phosphonium-hexafluorophosphate.

When R⁷ is a hydrogen atom, the above mentioned process for thepreparation of compound of general formula (I) wherein T represents O,may optionally be completed by a further step according to the followingreaction scheme (process P2):

-   -   in which:

R¹, R², R³, R⁴, R⁵, R⁶, Het, X, and n are as defined above;

R⁷² is a hydrogen atom, a C₁-C₆-alkyl or a C₃-C₇-cycloalkyl; and

L² is a leaving group chosen as being a halogen atom, a 4-methylphenylsulfonyloxy or a methylsulfonyloxy;

comprising the reaction of a compound of general formula (Ia) with acompound of general formula (IV) to provide a compound of generalformula (I).According to a further aspect according to the invention, there isprovided a process P3 for the preparation of a compound of formula (I),wherein T represents S, and illustrated according to the followingreaction scheme:

in which X, n, R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and Het are as defined above;

Process P3 can be performed in the presence of a thionating agent.Starting amide derivatives of formula (I) can be prepared according toprocesses P1 or P2. Suitable thionating agents for carrying out processP3 according to the invention can be sulphur (S), sulfhydric acid (H₂S),sodium sulfide (Na₂S), sodium hydrosulfide (NaHS), boron trisulfide(B₂S₃), bis(diethylaluminium) sulfide ((AlEt₂)₂S), ammonium sulfide((NH₄)₂S), phosphorous pentasulfide (P₂S₅), Lawesson's reagent(2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide) ora polymer-supported thionating reagent such as described in J. Chem.Soc. Perkin 1, (2001), 358.in the presence or in the absence, of a catalytic or stoechiometric ormore, quantity of a base such as an inorganic and organic base.Preference is given to using alkali metal carbonates, such as sodiumcarbonate, potassium carbonate, potassium bicarbonate, sodiumbicarbonate; heterocyclic aromatic bases, such as pyridine, picoline,lutidine, collidine; and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylaminopyridine or N-methylpiperidine.According to a further aspect according to the invention, there isprovided a process P4 for the preparation of compound of formula (I),wherein T represents N—R^(a), N—OR^(b), N—NR^(a)R^(b) or N—CN, andillustrated according to the following reaction scheme:

-   -   in which:

R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Het, X, and n are as defined above;

L³ being a chlorine atom;

comprising the reaction of a compound of general formula (II) with acompound of general formula (V) to provide a compound of general formula(I).N-substituted carboximidoyl chloride of formula (V) are known or can beprepared by known processes, for example as described in Houben-Weyl,“Methoden der organischen Chemie” (1985), E5/1, 628-633 and Patai, “Thechemistry of amidines and imidates” (1975), 296-301.Suitable acid binders for carrying out process P4 according to theinvention can be inorganic and organic bases that are customary for suchreactions. Preference is given to using alkaline earth metal or alkalimetal hydroxides, such as sodium hydroxide, calcium hydroxide, potassiumhydroxide or other ammonium hydroxide derivatives; alkali metalcarbonates, such as sodium carbonate, potassium carbonate, potassiumbicarbonate, sodium bicarbonate; alkali metal or alkaline earth metalacetates, such as sodium acetate, potassium acetate, calcium acetate;alkaline earth metal or alkali metal hydrides, such as sodium hydride orpotassium hydride; alkaline earth metal or alkali metal alcoolates, suchas sodium methylate, sodium ethylate, sodium propylate or potassiumt-butylate; and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline, pyridine,N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU); or apolymer-supported acid scavenger (for example as detailed inhttp://www.iris-biotech.de/downloads/scavengers.pdf). It is alsopossible to work in the absence of any additional acid binder.

The compound according to the present invention can be preparedaccording to the general processes of preparation described above. Itwill nevertheless be understood that, on the basis of his generalknowledge and of available publications, the skilled worker will be ableto adapt this method according to the specifics of each of thecompounds, which it is desired to synthesise.

On the basis of his general knowledge and of available publications, theskilled worker will also be able to prepare intermediate compound offormula (II) according to the present invention.

The present invention also relates to a fungicidal compositioncomprising an effective amount of an active material of general formula(I). Thus, according to the present invention, there is provided afungicidal composition comprising, as an active ingredient, an effectiveamount of a compound of general formula (I) as defined above and anagriculturally acceptable support, carrier or filler.

In the present specification, the term “support” denotes a natural orsynthetic, organic or inorganic material with which the active materialis combined to make it easier to apply, notably to the parts of theplant. This support is thus generally inert and should be agriculturallyacceptable. The support may be a solid or a liquid. Examples of suitablesupports include clays, natural or synthetic silicates, silica, resins,waxes, solid fertilisers, water, alcohols, in particular butanol,organic solvents, mineral and plant oils and derivatives thereof.Mixtures of such supports may also be used.

The composition may also comprise additional components. In particular,the composition may further comprise a surfactant. The surfactant can bean emulsifier, a dispersing agent or a wetting agent of ionic ornon-ionic type or a mixture of such surfactants. Mention may be made,for example, of polyacrylic acid salts, lignosulphonic acid salts,phenolsulphonic or naphthalenesulphonic acid salts, polycondensates ofethylene oxide with fatty alcohols or with fatty acids or with fattyamines, substituted phenols (in particular alkylphenols or arylphenols),salts of sulphosuccinic acid esters, taurine derivatives (in particularalkyl taurates), phosphoric esters of polyoxyethylated alcohols orphenols, fatty acid esters of polyols, and derivatives of the abovecompounds containing sulphate, sulphonate and phosphate functions. Thepresence of at least one surfactant is generally essential when theactive material and/or the inert support are water-insoluble and whenthe vector agent for the application is water. Preferably, surfactantcontent may be comprised between 5% and 40% by weight of thecomposition.

Optionally, additional components may also be included, e.g. protectivecolloids, adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active materialscan be combined with any solid or liquid additive, which complies withthe usual formulation techniques.

In general, the composition according to the invention may contain from0.05 to 99% (by weight) of active material, preferably 10 to 70% byweight.

Compositions according to the present invention can be used in variousforms such as aerosol dispenser, capsule suspension, cold foggingconcentrate, dustable powder, emulsifiable concentrate, emulsion oil inwater, emulsion water in oil, encapsulated granule, fine granule,flowable concentrate for seed treatment, gas (under pressure), gasgenerating product, granule, hot fogging concentrate, macrogranule,microgranule, oil dispersible powder, oil miscible flowable concentrate,oil miscible liquid, paste, plant rodlet, powder for dry seed treatment,seed coated with a pesticide, soluble concentrate, soluble powder,solution for seed treatment, suspension concentrate (flowableconcentrate), ultra low volume (ulv) liquid, ultra low volume (ulv)suspension, water dispersible granules or tablets, water dispersiblepowder for slurry treatment, water soluble granules or tablets, watersoluble powder for seed treatment and wettable powder.

These compositions include not only compositions which are ready to beapplied to the plant or seed to be treated by means of a suitabledevice, such as a spraying or dusting device, but also concentratedcommercial compositions which must be diluted before application to thecrop.

The compounds of the invention can also be mixed with one or moreinsecticides, fungicides, bactericides, attractant acaricides orpheromones or other compounds with biological activity. The mixturesthus obtained have a broadened spectrum of activity. The mixtures withother fungicides are particularly advantageous. Examples of suitablefungicide mixing partners may be selected in the following lists:

1) a compound capable to inhibit the nucleic acid synthesis likebenalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon,dimethirimol, ethirimol, furalaxyl, hymexazol, mefenoxam, metalaxyl,metalaxyl-M, ofurace, oxadixyl, oxolinic acid;

2) a compound capable to inhibit the mitosis and cell division likebenomyl, carbendazim, diethofencarb, ethaboxam, fuberidazole,pencycuron, thiabendazole thiophanate-methyl, zoxamide;

3) a compound capable to inhibit the respiration for example

as CI-respiration inhibitor like diflumetorim;

as CII-respiration inhibitor like boscalid, carboxin, fenfuram,flutolanil, furametpyr, furmecyclox, mepronil, oxycarboxine,penthiopyrad, thifluzamide; isopyrazam

as CIII-respiration inhibitor like amisulbrom, azoxystrobin, cyazofamid,dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin,kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin,pyraclostrobin, trifloxystrobin;

4) a compound capable of to act as an uncoupler like dinocap, fluazinam,meptyldinocap;

5) a compound capable to inhibit ATP production like fentin acetate,fentin chloride, fentin hydroxide, silthiofam;

6) a compound capable to inhibit AA and protein biosynthesis likeandoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycinhydrochloride hydrate, mepanipyrim, pyrimethanil;

7) a compound capable to inhibit the signal transduction likefenpiclonil, fludioxonil, quinoxyfen;

8) a compound capable to inhibit lipid and membrane synthesis likebiphenyl, chlozolinate, edifenphos, etridiazole, iodocarb, iprobenfos,iprodione, isoprothiolane, procymidone, propamocarb, propamocarbhydrochloride, pyrazophos, tolclofos-methyl, vinclozolin;

9) a compound capable to inhibit ergosterol biosynthesis like aldimorph,azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole,difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorphacetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole,fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol,fusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole,imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole,myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol,pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole,pyributicarb, pyrifenox, simeconazole, spiroxamine, tebuconazole,terbinafine, tetraconazole, triadimefon, triadimenol, tridemorph,triflumizole, triforine, triticonazole, uniconazole, viniconazole,voriconazole;

10) a compound capable to inhibit cell wall synthesis likebenthiavalicarb, bialaphos, dimethomorph, flumorph, iprovalicarb,mandipropamid, polyoxins, polyoxorim, validamycin A;

11) a compound capable to inhibit melanine biosynthesis likecarpropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole;

12) a compound capable to induce a host defence likeacibenzolar-S-methyl, probenazole, tiadinil;

13) a compound capable to have a multisite action like Bordeaux mixture,captafol, captan, chlorothalonil, copper naphthenate, copper oxide,copper oxychloride, copper preparations such as copper hydroxide, coppersulphate, dichlofluanid, dithianon, dodine, dodine free base, ferbam,fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine,iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb,maneb, metiram, metiram zinc, oxine-copper, propineb, sulphur andsulphur preparations including calcium polysulphide, thiram,tolylfluanid, zineb, ziram;

14) a compound selected in the following list:(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide,(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol,1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl-1H-imidazole-1-carboxylate,2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine,2-butoxy-6-iodo-3-propyl-4H-chromen-4-one,2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)nicotinamide,2-phenylphenol and salts, 3,4,5-trichloropyridine-2,6-dicarbonitrile,3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide,3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1R)-1,2,2-trimethylpropyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine,5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1, 2,4]triazolo[1,5-a]pyrimidin-7-amine, 8-hydroxyquinoline sulfate,benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, cufraneb,cyflufenamid, cymoxanil, dazomet, debacarb, dichlorophen, diclomezine,dicloran, difenzoquat, difenzoquat methylsulphate, diphenylamine,ferimzone, flumetover, fluopicolide, fluoroimide, flusulfamide,fluthianil, fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium,hexachlorobenzene, irumamycin, isotianil, methasulfocarb, methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}thio)methyl]phenyl}-3-methoxyacrylate,methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,methyl isothiocyanate, metrafenone, mildiomycin,N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide,N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N<-(methylsulfonyl)valinamide,N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-{2-[1,1′-bi(cyclopropyl)-2-yl]phenyl}-3-(difluoromethyl)-,1-methyl-1H-pyrazole-4-carboxamide,N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide,natamycin,N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide,N-ethyl-N-methyl-N′-{2-methyl-5-(difluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide,nickel dimethyldithiocarbamate, nitrothal-isopropyl,O-{1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl}1H-imidazole-1-carbothioate,octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts,phosphorous acid and its salts, piperalin, propamocarb fosetylate,propanosine-sodium, proquinazid, pyribencarb, pyrrolnitrine, quintozene,tecloftalam, tecnazene, triazoxide, trichlamide, valiphenal, zarilamid.

The composition according to the invention comprising a mixture of acompound of formula (I) with a bactericide compound may also beparticularly advantageous. Examples of suitable bactericide mixingpartners may be selected in the following list: bronopol, dichlorophen,nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone,furancarboxylic acid, oxytetracycline, probenazole, streptomycin,tecloftalam, copper sulphate and other copper preparations.

The fungicidal compositions of the present invention can be used tocuratively or preventively control the phytopathogenic fungi of crops.Thus, according to a further aspect of the present invention, there isprovided a method for curatively or preventively controlling thephytopathogenic fungi of crops characterised in that a fungicidalcomposition as hereinbefore defined is applied to the seed, the plantand/or to the fruit of the plant or to the soil in which the plant isgrowing or in which it is desired to grow.

The composition as used against phytopathogenic fungi of crops comprisesan effective and non-phytotoxic amount of an active material of generalformula (I).

The expression “effective and non-phytotoxic amount” means an amount ofcomposition according to the invention which is sufficient to control ordestroy the fungi present or liable to appear on the crops, and whichdoes not entail any appreciable symptom of phytotoxicity for the saidcrops. Such an amount can vary within a wide range depending on thefungus to be controlled, the type of crop, the climatic conditions andthe compounds included in the fungicidal composition according to theinvention.

This amount can be determined by systematic field trials, which arewithin the capabilities of a person skilled in the art.

The method of treatment according to the present invention is useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.This method of treatment can also be useful to treat roots. The methodof treatment according to the present invention can also be useful totreat the overground parts of the plant such as trunks, stems or stalks,leaves, flowers and fruits of the concerned plant.

Among the plants that can be protected by the method according to thepresent invention, mention may be made of cotton; flax; vine; fruit orvegetable crops such as Rosaceae sp. (for instance pip fruit such asapples and pears, but also stone fruit such as apricots, almonds andpeaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp.,Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp.,Actimidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana treesand plantins), Rubiaceae sp., Theaceae sp., Sterculiceae sp., Rutaceaesp. (for instance lemons, oranges and grapefruit); Solanaceae sp. (forinstance tomatoes), Liliaceae sp., Asteraceae sp. (for instancelettuces), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp.,Cucurbitaceae sp., Papilionaceae sp. (for instance peas), Rosaceae sp.(for instance strawberries); major crops such as Graminae sp. (forinstance maize, lawn or cereals such as wheat, rice, barley andtriticale), Asteraceae sp. (for instance sunflower), Cruciferae sp. (forinstance colza), Fabacae sp. (for instance peanuts), Papilionaceae sp.(for instance soybean), Solanaceae sp. (for instance potatoes),Chenopodiaceae sp. (for instance beetroots); horticultural and forestcrops; as well as genetically modified homologues of these crops.

Among the diseases of plants or crops that can be controlled by themethod according to the present invention, mention may be made of:

Powdery mildew diseases such as:

Blumeria diseases, caused for example by Blumeria graminis;

Podosphaera diseases, caused for example by Podosphaera leucotricha;

Sphaerotheca diseases, caused for example by Sphaerotheca fuliginea;

Uncinula diseases, caused for example by Uncinula necator,

Rust diseases such as:

Gymnosporangium diseases, caused for example by Gymnosporangium sabinae;

Hemileia diseases, caused for example by Hemileia vastatrix;

Phakopsora diseases, caused for example by Phakopsora pachyrhizi orPhakopsora meibomiae;

Puccinia diseases, caused for example by Puccinia recondite;

Uromyces diseases, caused for example by Uromyces appendiculatus;

Oomycete diseases such as:

Bremia diseases, caused for example by Bremia lactucae;

Peronospora diseases, caused for example by Peronospora pisi or P.brassicae;

Phytophthora diseases, caused for example by Phytophthora infestans;

Plasmopara diseases, caused for example by Plasmopara viticola;

Pseudoperonospora diseases, caused for example by Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Pythium diseases, caused for example by Pythium ultimum;

Leafspot, leaf blotch and leaf blight diseases such as:

Alternaria diseases, caused for example by Alternaria solani;

Cercospora diseases, caused for example by Cercospora beticola;

Cladiosporum diseases, caused for example by Cladiosporium cucumerinum;

Cochliobolus diseases, caused for example by Cochliobolus sativus;

Colletotrichum diseases, caused for example by Colletotrichumlindemuthanium;

Cycloconium diseases, caused for example by Cycloconium oleaginum;

Diaporthe diseases, caused for example by Diaporthe citri;

Elsinoe diseases, caused for example by Elsinoe fawcettii;

Gloeosporium diseases, caused for example by Gloeosporium laeticolor,

Glomerella diseases, caused for example by Glomerella cingulata;

Guignardia diseases, caused for example by Guignardia bidwelli;

Leptosphaeria diseases, caused for example by Leptosphaeria maculans;Leptosphaeria nodorum;

Magnaporthe diseases, caused for example by Magnaporthe grisea;

Mycosphaerella diseases, caused for example by Mycosphaerellagraminicola; Mycosphaerella arachidicola; Mycosphaerella fijiensis;

Phaeosphaeria diseases, caused for example by Phaeosphaeria nodorum;

Pyrenophora diseases, caused for example by Pyrenophora teres;

Ramularia diseases, caused for example by Ramularia collo-cygni;

Rhynchosporium diseases, caused for example by Rhynchosporium secalis;

Septoria diseases, caused for example by Septoria apii or Septorialycopercisi;

Typhula diseases, caused for example by Typhula incarnate;

Venturia diseases, caused for example by Venturia inaequalis;

Root and stem diseases such as:

Corticium diseases, caused for example by Corticium graminearum;

Fusarium diseases, caused for example by Fusarium oxysporum;

Gaeumannomyces diseases, caused for example by Gaeumannomyces graminis;

Rhizoctonia diseases, caused for example by Rhizoctonia solani;

Tapesia diseases, caused for example by Tapesia acuformis;

Thielaviopsis diseases, caused for example by Thielaviopsis basicola;

Ear and panicle diseases such as:

Alternaria diseases, caused for example by Alternaria spp.;

Aspergillus diseases, caused for example by Aspergillus flavus;

Cladosporium diseases, caused for example by Cladosporium spp.;

Claviceps diseases, caused for example by Claviceps purpurea;

Fusarium diseases, caused for example by Fusarium culmorum;

Gibberella diseases, caused for example by Gibberella zeae;

Monographella diseases, caused for example by Monographella nivalis;

Smut and bunt diseases such as:

Sphacelotheca diseases, caused for example by Sphacelotheca reiliana;

Tilletia diseases, caused for example by Tilletia caries;

Urocystis diseases, caused for example by Urocystis occulta;

Ustilago diseases, caused for example by Ustilago nuda;

Fruit rot and mould diseases such as:

Aspergillus diseases, caused for example by Aspergillus flavus;

Botrytis diseases, caused for example by Botrytis cinerea;

Penicillium diseases, caused for example by Penicillium expansum;

Sclerotinia diseases, caused for example by Sclerotinia sclerotiorum;

Verticilium diseases, caused for example by Verticilium alboatrum;

Seed and soilborne decay, mould, wilt, rot and damping-off diseases:

Fusarium diseases, caused for example by Fusarium culmorum;

Phytophthora diseases, caused for example by Phytophthora cactorum;

Pythium diseases, caused for example by Pythium ultimum;

Rhizoctonia diseases, caused for example by Rhizoctonia solani;

Sclerotium diseases, caused for example by Sclerotium rolfsii;

Microdochium diseases, caused for example by Microdochium nivale;

Canker, broom and dieback diseases such as:

Nectria diseases, caused for example by Nectria galligena;

Blight diseases such as:

Monilinia diseases, caused for example by Monilinia taxa;

Leaf blister or leaf curl diseases such as:

Taphrina diseases, caused for example by Taphrina deformans;

Decline diseases of wooden plants such as:

Esca diseases, caused for example by Phaemoniella clamydospora;

Diseases of flowers and Seeds such as:

Botrytis diseases, caused for example by Botrytis cinerea;

Diseases of tubers such as:

Rhizoctonia diseases, caused for example by Rhizoctonia solani;

Helminthosporium diseases, caused for example by Helminthosporium

The fungicide composition according to the present invention may also beused against fungal diseases liable to grow on or inside timber. Theterm “timber” means all types of species of wood, and all types ofworking of this wood intended for construction, for example solid wood,high-density wood, laminated wood, and plywood. The method for treatingtimber according to the invention mainly consists in contacting one ormore compounds of the present invention, or a composition according tothe invention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

The dose of active material usually applied in the treatment accordingto the present invention is generally and advantageously between 10 and800 g/ha, preferably between 50 and 300 g/ha for applications in foliartreatment. The dose of active substance applied is generally andadvantageously between 2 and 200 g per 100 kg of seed, preferablybetween 3 and 150 g per 100 kg of seed in the case of seed treatment. Itis clearly understood that the doses indicated above are given asillustrative examples of the invention. A person skilled in the art willknow how to adapt the application doses according to the nature of thecrop to be treated.

The fungicidal composition according to the present invention may alsobe used in the treatment of genetically modified organisms with thecompounds according to the invention or the agrochemical compositionsaccording to the invention. Genetically modified plants are plants intowhose genome a heterologous gene encoding a protein of interest has beenstably integrated. The expression “heterologous gene encoding a proteinof interest” essentially means genes which give the transformed plantnew agronomic properties, or genes for improving the agronomic qualityof the transformed plant.

The compositions according to the present invention may also be used forthe preparation of composition useful to curatively or preventivelytreat human and animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp., for example Aspergillus fumigatus.

The aspects of the present invention will now be illustrated withreference to the following tables of compounds and examples. Thefollowing Table illustrates in a non-limiting manner examples offungicidal compounds according to the present invention. In thefollowing Examples, M+1 (or M−1) means the molecular ion peak, plus orminus 1 a.m.u. (atomic mass units) respectively, as observed in massspectroscopy and M (Apcl+) means the molecular ion peak as it was foundvia positive atmospheric pressure chemical ionisation in massspectroscopy.

TABLE A

Compound R¹ R² R³ R⁴ R⁵ R⁶ R⁷ X¹ X² X³ X⁴ X⁵ T Y¹ Y² Y^(a) (M + 1) A-1 HH H H H H H Cl H Cl H H O H H CF₃ 382 A-2 H H H H H H H Cl H Cl H H O HH I 440 A-3 H H H H H H H Cl H Cl H H O H H Me 328

TABLE B

Compound R¹ R² R³ R⁴ R⁵ R⁶ R⁷ X¹ X² X³ X⁴ X⁵ T Y¹ Y² Q Y^(a) (M + 1) B-1H H H H H H H Cl H Cl H H O H H S CF₃ 400

TABLE C

Compound R¹ R² R³ R⁴ R⁵ R⁶ R⁷ X¹ X² X³ X⁴ X⁵ T Y¹ Y^(a) (M + 1) C-1 H HH H H H H Cl H Cl H H O Me CHF₂ 379

TABLE D

Compound R¹ R² R³ R⁴ R⁵ R⁶ R⁷ X¹ X² X³ X⁴ X⁵ T Y¹ Y² Y³ Y^(a) (M + 1)D-1 H H H H H H H Cl H Cl H H O H H H Cl 343

TABLE E

Compound R¹ R² R³ R⁴ R⁵ R⁶ R⁷ X¹ X² X³ X⁴ X⁵ T Y¹ Y² Y^(a) (M + 1) E-1 HH H H H H H Cl H Cl H H O F Me Me 344 E-2 H H H H H H H Cl H Cl H H O FMe CF₃ 398 E-3 H H H H H H H Cl H Cl H H O H Me Et 340 E-4 H H H H H H HCl H Cl H H O H Me EtO 356 E-5 H H H H H H H Cl H Cl H H O H Me CF₃ 380E-6 H H H H H H H Cl H Cl H H O H Me CHF₂ 362 E-7 H H H H H H H Cl H ClH H O H Me MeO 342 E-8 H H H H H H H Cl H Cl H H O H Me I 438 E-9 H H HH H H H Cl H Cl H H O Cl Me Me 360 E-10 H H H H H Me cPr Cl H Cl H H O FMe Me 398 E-11 Me H H H H H cPr H H H H H O F Me Me 330 E-12 H H H H HMe cPr CF3 H H H H O F Me Me 398 E-13 H H H H H Me cPr H Cl Cl H H O FMe Me 398 E-14 H H H H H Me cPr H Cl Cl H H S F Me Me 414

TABLE F

Compound R¹ R² R³ R⁴ R⁵ R⁶ R⁷ X¹ X² X³ X⁴ X⁵ T Y¹ Y² Y³ Y^(a) (M + 1)F-1 H H H H H H H Cl H Cl H H O H H H CF₃ 377

TABLE G

Compound R¹ R² R³ R⁴ R⁵ R⁶ R⁷ X¹ X² X³ X⁴ X⁵ T Y¹ Y² (M + 1) G-1 H H H HH H H Cl H Cl H H O Cl Cl 383

TABLE H

Compound R¹ R² R³ R⁴ R⁵ R⁶ R⁷ X¹ X² X³ X⁴ X⁵ T Y¹ Y² Y^(a) (M + 1) H-1 HH H H H H H Cl H Cl H H O Me Et Br 419

EXAMPLES OF PROCESS FOR THE PREPARATION OF THE COMPOUND OF GENERALFORMULA (I) Preparation ofN-[3-(2,4-dichlorophenyl)propyl]-3-iodothiophene-2-carboxa-mide(compound A-2)

3-iodothiophene-2-carboxylic acid (411 mg, 1.617 mmol), DMF (0.002 ml,0.026 mmol) and thionyl chloride (2 mml, 27.42 mmol) are stirred at 80°C. for two hours. The reaction mixture was concentrated in vacuo and thecrude product was diluted in dichloromethane (2 ml), added to a mixtureof 3-(2,4-dichlorophenyl)propan-1-amine (3000 mg, 1.47 mmol) andtriethylamine (246 μl, 1.34 mmol) in dichloromethane (5 ml). Thereaction mixture was stirred for 48 hours at room temperature.

The reaction mixture was filtered through a plug of basic alumina.

The filtrate was concentrated in vacuo, purified by flash chromatographyon silica (ethyl acetate/heptane) to yield toN-[3-(2,4-dichlorophenyl)propyl]-3-iodothiophene-2-carboxamide: 314 mg(42%).

Mass spectrum: 440 (M+1).

General Preparation: Thionation of an Amide Derivative of Formula (I) onChemspeed™ Apparatus

In a 13 ml Chemspeed™ vial is weighted 0.27 mmole of phosphorouspentasulfide (P₂S₅). 3 ml of a 0.18 molar solution of the amide (1)(0.54 mmole) in dioxane is added and the mixture is heated at reflux fortwo hours. The temperature is then cooled to 80° C. and 2.5 ml of waterare added. The mixture is heated at 80° C. for one more hour. 2 ml ofwater are then added and the reaction mixture is extracted twice by 4 mlof dichloromethane. The organic phase is deposited on a basic aluminacardridge (2 g) and eluted twice by 8 ml of dichloromethane. Thesolvents are removed and the crude thioamide is analyzed by LCMS andNMR. Insufficiently pure compounds are further purified by preparativeLCMS.

Examples of Biological Activity of the Compound of General Formula (I)Example A In Vivo Test on Sphaerotheca fuliginea (Powdery Mildew)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Vert petit de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 20° C./23° C., aretreated at the cotyledon Z11 stage by spraying with the aqueoussuspension described above. Plants, used as controls, are treated withan aqueous solution not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Sphaerotheca fuliginea spores (100 000 spores perml). The spores are collected from a contaminated plants. Thecontaminated gerkhin plants are incubated at about 20° C./25° C. and at60/70% relative humidity.

Grading (% of efficacy) is carried out 21 days after the contamination,in comparison with the control plants.

Under these conditions, good (at least 70%) or total protection isobserved at a dose of 500 ppm with the following compounds: A2, C1, E2,E5, E6, E8 and F1.

Example B In Vivo Test on Pyrenophora teres (Barley Net Blotch)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, then diluted with water to obtain thedesired active material concentration.

Barley plants (Express variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the active ingredient prepared asdescribed above. Plants, used as controls, are treated with the mixtureof acetone/tween/DMSO/water not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Pyrenophora teres spores (12,000 spores per ml).The spores are collected from a 12-day-old culture. The contaminatedbarley plants are incubated for 24 hours at about 20° C. and at 100%relative humidity, and then for 12 days at 80% relative humidity.

Grading is carried out 12 days after the contamination, in comparisonwith the control plants.

Under these conditions, good (at least 70%) or total protection isobserved at a dose of 500 ppm with the following compounds: B1, C1, E5,E6, E8, E9 and F1.

Example C In Vivo Test on Alternaria brassicae (Leaf Spot of Crucifers)

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Radish plants (Pernot variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 18-20° C., are treated at thecotyledon stage by spraying with the active ingredient prepared asdescribed above.

Plants, used as controls, are treated with the mixture ofacetone/tween/water not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Alternaria brassicae spores (40,000 spores percm³). The spores are collected from a 12 to 13 days-old culture.

The contaminated radish plants are incubated for 6-7 days at about 18°C., under a humid atmosphere.

Grading is carried out 6 to 7 days after the contamination, incomparison with the control plants.

Under these conditions, good protection (at least 70%) is observed at adose of 500 ppm with the following compounds: C1, D1, E1, E5, E6 and E9.

Example D Cell Test on Mycosphaerella graminicola

The growth of Mycosphaerella graminicola is performed in a bactopeptonebased liquid medium at 20° C. under shaking (120 rpm) during 72 hours.The bactopeptone based medium is prepared by mixing 14.6 grams ofD-glucose, 1.4 grams of Yeast extract and 7.1 g of bacteriologicalpeptone (OXOID ref. LP0037) in 1 liter of demineralized water. Themedium is sterilized by autoclave 15 minutes at 121° C. After 72 hours,pre-culture of Mycosphaerella graminicola is recovered and the opticdensity (OD) at 620 nm is adjusted with the bactopeptone based medium at0.5. The compounds are dissolved in DMSO and added to sterile liquidbactopeptone medium at a concentration of 6 ppm. The medium isinoculated with the pre-culture of Mycosphaerella graminicola by adilution of 10 times of the pre-culture. The efficacy of the compoundsis assessed by OD measurement at 620 nm after 4 days at 20° C. incomparison with a control.

Under these conditions, the following compounds showed good (at least70%) protection at the dose of 6 ppm.: A1, A2, B1, C1, D1, E1, E2, E5,E6, and F1.

Under similar conditions,N-(3,3-diphenylpropyl)-3-hydroxy-4-methoxypyridine-2-carboxamide (i.e.compound 16 disclosed in International Patent Application WO 00/76979)and(3-(4-chlorophenyl)-N-[3-(3,4-dimethoxyphenyl)propyl]-5-methylisoxazole-4-carboxamide)(i.e. compound 60 disclosed in International Patent Application WO2005/066138) did not show any activity.

1. A compound of general formula (I)

in which: n is 1, 2, 3, 4 or 5; T represents O, S, N—R^(a), N—OR^(b),N—NR^(a)R^(b) or N—CN; X is a halogen atom, a nitro group, a cyanogroup, a hydroxy group, an amino group, a sulfanyl group, apentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxy group, aformylamino group, a carboxy group, a carbamoyl group, aN-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₁-C₈-alkylamino, a di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, aC₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, a C₁-C₈-alkylsulfanyl,a C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, aC₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogenatoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5halogen atoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to 5halogen atoms, a C₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylsulphonyl, aC₁-C₈-halogenoalkylsulphonyl having 1 to 5 halogen atoms, aC₁-C₆-alkoxyimino, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a (benzyloxyimino)-C₁-C₆-alkyl, abenzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanylor a phenylamino; R¹ and R² are chosen independently of each other asbeing a hydrogen atom, a halogen atom, a C₁-C₈-halogenoalkyl having 1 to5 halogen atoms, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5 halogenatoms, a C₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; R³ and R⁴ are chosenindependently of each other as being a hydrogen atom, a halogen atom, aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₈-alkyl, aC₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; R⁵ and R⁶ are chosenindependently of each other as being a hydrogen atom, aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₈-alkyl, aC₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; R⁷ is a hydrogenatom, a C₁-C₆-alkyl or a C₃-C₇-cycloalkyl; R^(a) and R^(b), that can bethe same or different, represent a hydrogen atom; C₁-C₈-alkyl;C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₂-C₈-alkenyl;C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be thesame or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to9 halogen atoms that can be the same or different; C₃-C₇-cycloalkyl;C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-halogenocycloalkyl comprising up to9 halogen atoms that can be the same or different; formyl;C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising up to 9halogen atoms that can be the same or different; C₁-C₈-alkylsulphonyl;C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms that canbe the same or different; phenyl that can be substituted by up to 5groups Q; naphthyl that can be substituted by up to 6 groups Q;phenylmethylene that can be substituted by up to 5 groups Q;phenylsulphonyl that can be substituted by up to 5 groups Q; Q, that canbe the same or different, represents a halogen atom; cyano; nitro;C₁-C₈-alkyl; C₁-C₈-alkoxy; C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; tri(C₁-C₈)alkylsilyl andtri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl; C₁-C₈-alkoxyimino;(C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; and Het represents a 5-, 6- or7-membered non-fused heterocycle with one, two or three heteroatomswhich may be the same or different, Het being linked by a carbon atomand Het being substituted in ortho-position by at least one substituantlinked by a carbon atom and optionally substituted in any other positionby one or further substituents chosen from a halogen atom, a nitrogroup, a pentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxygroup, a formylamino group, a carboxy group, a C₁-C₈-alkyl, aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkoxy having 1 to 5halogen atoms, a C₁-C₈-alkoxy-C₂-C₈-alkenyl, a C₁-C₈-alkylsulfanyl, aC₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to 5halogen atoms, a C₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylsulphonyl, aC₁-C₈-halogenoalkylsulphonyl having 1 to 5 halogen atoms or aC₁-C₈-alkylsulfonamide; as well as its salts, N-oxydes, metalliccomplexes, metalloidic complexes and optically active isomers; with theproviso that compound of formula (I) is different from:4,6-dichloro-2-(methylthio)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,4-chloro-2-(methylthio)-6-[(2-phenylethyl)amino]-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,4-chloro-2-(methylthio)-6-[(2-phenylmethyl)amino]-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,4-chloro-2-(methylthio)-6-(phenylamino)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,4-chloro-2-(methylthio)-6-[(2-phenylpropyl)amino]-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,5-chloro-1-methyl-N-(3-phenylpropyl)-1H-pyrazole-4-carboxamide,N-[3-(4-acetylphenyl)propyl]-5-chloro-3-methoxythiophene-2-carboxamide,and 4-(3-{[(5-chloro-3-methoxy-2-thienyl)carbonyl]amino}propyl)benzoicacid.
 2. A compound according to claim 1, characterised in that n is 1or
 2. 3. A compound according to claim 1, characterised in that X ischosen as being a halogen atom, a (hydroxyimino)-C₁-C₆-alkyl group, aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₈-alkyl, aC₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₁-C₈-halogenoalkoxy having 1 to 5halogen atoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1to 5 halogen atoms, a C₁-C₆-alkoxyimino, a(C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl,a (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl or a (benzyloxyimino)-C₁-C₆-alkyl.4. A compound according to claim 1, characterised in that R¹ and R² arechosen independently of each other as being a hydrogen atom or aC₁-C₈-alkyl.
 5. A compound according to claim 1, characterised in thatR³ and R⁴ are chosen independently of each other as being a hydrogenatom or a C₁-C₈-alkyl.
 6. A compound according to claim 1, characterisedin that R⁵ and R⁶ are chosen independently of each other as being ahydrogen atom or a C₁-C₈-alkyl.
 7. A compound according to claim 1,characterised in that Het is chosen as being 2-furan, 3-furan,4,5-dihydro-3-furan, 2-thiophene, 3-thiophene, 2-pyrrole, 3-pyrrole,5-oxazole, 4-oxazole, 5-thiazole, 4-thiazole, 5-pyrazole, 4-pyrazole,3-pyrazole, 3-isoxazole, 4-isoxazole, 5-isoxazole, 4-isothiazole,4-1,2,3-triazole, 4-thiadiazole, 5-1,2,3-thiadiazole,4,5-dihydro-4-pyrazole, 2-pyridine, 3-pyridine, 4-pyridine,1,4-oxathiine, 3,4-dihydro-5-pyran, 2,3-dihydro-1,4-oxathiine, or2-pyrazine
 8. A compound according to claim 1, characterised in that Hetis substituted in ortho position by a halogen atom, a C₁-C₈-alkyl or aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms.
 9. A compound accordingto claim 1, characterised in that Het is substituted in any positiondifferent to the ortho position by a hydrogen atom, a halogen atom, aC₁-C₆-alkyl, an amino group, a C₁-C₈-alkylamino or adi-C₁-C₈-alkylamino.
 10. A compound according to claim 1, characterisedin that Het is a 5-membered heterocycle.
 11. A compound according toclaim 1, characterised in that Het is a 6-membered heterocycle.
 12. Acompound according to claim 1, characterised in that R⁷ is hydrogen. 13.A compound according to claim 1, characterised in that R⁷ iscyclopropyl.
 14. A compound according to claim 1, characterised in thatT is oxygen.
 15. A compound according to claim 1, characterised in thatT is sulfur.
 16. A process for the preparation of a compound of generalformula (I) as defined in claim 1, which comprises reacting a3-phenylpropan-1-amine derivative of general formula (II) or one of itssalt:

in which n is 1, 2, 3, 4 or 5; X is a halogen atom, a nitro group, acyano group, a hydroxy group, an amino group, a sulfanyl group, apentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxy group, aformylamino group, a carboxy group, a carbamoyl group, aN-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₁-C₈-alkylamino, a di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, aC₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, a C₁-C₈-alkylsulfanyl,a C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, aC₁-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogenatoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5halogen atoms a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to5 halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈: alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to 5halogen atoms a C₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinylhaving 1 to 5 halogen atoms, a C₁-C₈: alkylsulphonyl, aC₁-C₈-halogenoalkylsulphonyl having 1 to 5 halogen atoms, aC₁-C₆-alkoxyimino, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a (benzyloxyimino)-C₁-C₆-alkyl, abenzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanylor a phenylamino; R¹ and R² are chosen independently of each other asbeing a hydrogen atom, a halogen atom, a C₁-C₈-halogenoalkyl having 1 to5 halogen atoms, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₁-C₈-alkynyl, aC₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5 halogenatoms, a C₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; R³ and R⁴ are chosenindependently of each other as being a hydrogen atom, a halogen atom, aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₈-alkyl, aC₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; R⁵ and R⁶ are chosenindependently of each other as being a hydrogen atom, aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₈-alkyl, aC₂-C₈-alkenyl, a C₁-C₈-alkynyl, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; and R⁷ is a hydrogenatom, a C₁-C₆-alkyl or a C₃-C₇-cycloalkyl; with a carboxylic acidderivative of the general formula (III)

in which: Het represents a 5-, 6- or 7-membered non-fused heterocyclewith one, two or three heteroatoms which may be the same or different,Het being linked by a carbon atom and Het being substituted inortho-position by at least one substituant linked by a carbon atom andoptionally substituted in any other position by one or furthersubstituents chosen from a halogen atom, a nitro group, apentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxy group, aformylamino group, a carboxy group, a C₁-C₈-alkyl, a C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms, a C₂-C₈-alkenyl, a C₁-C₈-alkynyl, aC₁-C₈-alkoxy, a C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, aC₁-C₈-alkoxy-C₇-C₈-alkenyl, a C₁-C₈-alkylsulfanyl, aC₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to 5halogen atoms, a C₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylsulphonyl, aC₁-C₈-halogenoalkylsulphonyl having 1 to 5 halogen atoms or aC₁-C₈-alkylsulfonamide; and L is a leaving group chosen as being ahalogen atom, a hydroxyl group, —OR^(a), —OCOR^(a), R^(a) being a C₁-C₆alkyl, a C₁-C₆ haloalkyl, a benzyl, 4-methoxybenzyl, pentafluorophenylor a group of formula

in the presence of a catalyst and, if L is a hydroxyl group, in thepresence of a condensing agent.
 17. A process according to claim 16,characterised in that R⁷ is a hydrogen atom and that the process iscompleted by a further step according to the following reaction scheme:

in which: R¹ and R² are chosen independently of each other as being ahydrogen atom, a halogen atom, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5 halogenatoms, a C₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; R³ and R⁴ are chosenindependently of each other as being a hydrogen atom, a halogen atom aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₈-alkyl, aC₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; R⁵ and R⁶ are chosenindependently of each other as being a hydrogen atom, aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₈-alkyl, aC₁-C₈-alkenyl, a C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; Het represents a 5-,6- or 7-membered non-fused heterocycle with one, two or threeheteroatoms which may be the same or different, Het being linked by acarbon atom and Het being substituted in ortho-position by at least onesubstituant linked by a carbon atom and optionally substituted in anyother position by one or further substituents chosen from a halogenatom, a nitro group, a pentafluoro-λ⁶-sulfanyl group, a formyl group, aformyloxy group, a formylamino group, a carboxy group, a C₁-C₈-alkyl, aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, aC₁-C₈-alkynyl, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkoxy having 1 to 5halogen atoms, a C₁-C₈-alkoxy-C₂-C₈-alkenyl, a C₁-C₈-alkylsulfanyl, aC₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl haying 1 to 5halogen atoms, a C₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylsulphonyl, aC₁-C₈-halogenoalkylsulphonyl having 1 to 5 halogen atoms or aC₁-C₈-alkylsulfonamide; X is a halogen atom, a nitro group, a cyanogroup, a hydroxy group, an amino group, a sulfanyl group, apentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxy group, aformylamino group, a carboxy group, a carbamoyl group, aN-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₁-C₈-alkylamino, a di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, aC₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, a C₁-C₈=alkylsulfanyl,a C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, aC₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogenatoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5halogen atoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to 5halogen atoms, a C₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylsulphonyl, aC₁-C₈-halogenoalkylsulphonyl having 1 to 5 halogen atoms, aC₁-C₆-alkoxyimino, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a (benzyloxyimino)-C₁-C₆-alkyl, abenzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanylor a phenylamino; n is 1, 2, 3, 4 or 5; R^(7a) is a hydrogen atom, aC₁-C₆-alkyl or a C₃-C₇-cycloalkyl; and L¹ is a leaving group chosen asbeing a halogen atom, a 4-methyl phenylsulfonyloxy or amethylsulfonyloxy; comprising the reaction of a compound of generalformula (Ia) with a compound of general formula (III) to provide acompound of general formula (I).
 18. A fungicide composition comprisingan effective amount of a compound according to claim 1 and anagriculturally acceptable support.
 19. A method for preventively orcuratively combating the phytopathogenic fungi of crops, characterisedin that an effective and non-phytotoxic amount of a compositionaccording to claim 18 is applied to the plant seeds or to the plantleaves and/or to the fruits of the plants or to the soil in which theplants are growing or in which it is desired to grow them.
 20. A methodfor preventively or curatively combating the phytopathogenic fungi ofcrops, characterised in that an effective and non-phytotoxic amount of acompound according to claim 1 is applied to the plant seeds or to theplant leaves and/or to the fruits of the plants or to the soil in whichthe plants are growing or in which it is desired to grow them.